N-Methyl-3,5-dinitro­benzamide

Deng, G.-M.; Wang, C.-R.; Chen, Z.; Zhang, H.-M.

doi:10.1107/S1600536811053888

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o209

doi:10.1107/S1600536811053888

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N-Methyl-3,5-dinitrobenzamide

Gui-Ming Deng,^a,^b Chao-Run Wang,^b Zhen Chen ^b and He-Ming Zhang ^a ^*

^aMOE Key Laboratory of Laser Life Science & Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, People's Republic of China, and ^bThe First Affiliated Hospital of Hunan University of Chinese Medicine, Changsha 410007, People's Republic of China
^*Correspondence e-mail: zhang_heming88@yahoo.com.cn

(Received 12 December 2011; accepted 14 December 2011; online 21 December 2011)

The asymmetric unit of the title compound, C₈H₇N₃O₅, contains two independent molecules in which the amide plane is oriented at dihedral angles of 29.82 (2) and 31.17 (2)° with respect to the benzene ring. In the crystal, molecules are connected via intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For general background to the biological activity of benzamide derivatives, see: Lee et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₈H₇N₃O₅
M_r = 225.16
Orthorhombic, P b c a
a = 10.716 (2) Å
b = 10.057 (2) Å
c = 36.101 (7) Å
V = 3890.6 (13) Å³
Z = 16
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.962, T_max = 0.987
4711 measured reflections
3402 independent reflections
1653 reflections with I > 2σ(I)
R_int = 0.0582
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.162
S = 0.96
3402 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5ⁱ	0.86	2.06	2.900 (4)	165
N6—H6A⋯O10ⁱ	0.86	2.12	2.955 (4)	164
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053888/xu5409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053888/xu5409Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053888/xu5409Isup3.cml

checkCIF report

Comment top

Benzamide derivatives exhibit interesting biological activities such as antibacterial and antifungal effects (Lee et al.., 2009). We report here the crystal structure of the title compound (Fig. 1). Bond lengths and angles are within normal ranges (Allen et al., 1987).

In the crystal packing of (I) the molecules are connected together via N—H···O intermolecular hydrogen bonds to form a one-dimensional chains in the b direction (Table 1, graph set C1,1(4)), which seems to be very effective in the stabilization of the crystal structure.

Related literature top

For general background to the biological activity of benzamide derivatives, see: Lee et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A 1:1 mixture of N,N'-dimethylurea (0.088 g, 1 mmol), 3,5-dinitrobenzoic acid (0.212 g, 1 mmol) and ZrOCl₂.8H₂O (0.032 g, 1 mmol) were ground in a mortar, placed in a 50 ml conical flask and irradiated in a microwave oven. The progress of the reaction was monitored by TLC. After completion of the reaction, the contents were extracted with EtOAc (3 × 10 ml) and filtered to remove the catalyst. To remove unreacted acid, the organic layer was washed with a NaHCO₃ solution followed by water. Evaporating the organic solvent provided the crystals.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) (thermal ellipsoids are shown at 30% probability levels).
	Fig. 2. The packing of (I), viewed down the b axis. The dashed lines represent the hydrogen bonding interactions.

N-Methyl-3,5-dinitrobenzamide top

Crystal data top

C₈H₇N₃O₅	F(000) = 1856
M_r = 225.16	D_x = 1.538 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 10.716 (2) Å	θ = 9–13°
b = 10.057 (2) Å	µ = 0.13 mm⁻¹
c = 36.101 (7) Å	T = 293 K
V = 3890.6 (13) Å³	Block, yellow
Z = 16	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1653 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 25.1°, θ_min = 2.2°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
T_min = 0.962, T_max = 0.987	l = 0→42
4711 measured reflections	3 standard reflections every 200 reflections
3402 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0619P)²] where P = (F_o² + 2F_c²)/3
3402 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₈H₇N₃O₅	V = 3890.6 (13) Å³
M_r = 225.16	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 10.716 (2) Å	µ = 0.13 mm⁻¹
b = 10.057 (2) Å	T = 293 K
c = 36.101 (7) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1653 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.058
T_min = 0.962, T_max = 0.987	3 standard reflections every 200 reflections
4711 measured reflections	intensity decay: 1%
3402 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 0.96	Δρ_max = 0.21 e Å⁻³
3402 reflections	Δρ_min = −0.17 e Å⁻³
289 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	1.1588 (3)	0.7222 (4)	0.65015 (10)	0.0554 (9)
C1	0.9707 (3)	0.8426 (4)	0.67035 (11)	0.0444 (10)
H1A	0.9221	0.7795	0.6582	0.053*
O1	1.0927 (3)	0.6404 (3)	0.63547 (10)	0.0798 (11)
O2	1.2734 (2)	0.7187 (3)	0.64960 (8)	0.0716 (9)
C2	1.0989 (3)	0.8326 (4)	0.67030 (11)	0.0462 (10)
N2	1.1949 (4)	1.1247 (4)	0.72609 (10)	0.0571 (10)
N3	0.7009 (3)	0.8718 (3)	0.68582 (10)	0.0568 (10)
H3A	0.7314	0.7927	0.6850	0.068*
O3	1.3077 (3)	1.1073 (3)	0.72618 (9)	0.0726 (10)
C3	1.1751 (3)	0.9227 (4)	0.68860 (12)	0.0521 (11)
H3B	1.2616	0.9148	0.6885	0.063*
O4	1.1423 (3)	1.2198 (3)	0.74015 (10)	0.0745 (10)
C4	1.1155 (3)	1.0243 (4)	0.70688 (12)	0.0461 (10)
O5	0.7395 (2)	1.0907 (2)	0.68914 (9)	0.0636 (9)
C5	0.9889 (3)	1.0400 (4)	0.70711 (11)	0.0437 (10)
H5A	0.9527	1.1114	0.7194	0.052*
C6	0.9151 (3)	0.9481 (3)	0.68874 (10)	0.0413 (10)
C7	0.7776 (3)	0.9749 (4)	0.68801 (11)	0.0445 (10)
C8	0.5670 (3)	0.8895 (4)	0.68472 (14)	0.0705 (14)
H8A	0.5272	0.8042	0.6832	0.106*
H8B	0.5450	0.9416	0.6634	0.106*
H8C	0.5401	0.9344	0.7068	0.106*
O6	0.3317 (3)	0.2716 (3)	0.39302 (10)	0.0788 (11)
O7	0.1844 (3)	0.1345 (4)	0.40663 (10)	0.0918 (12)
O8	0.2726 (3)	−0.2445 (4)	0.48397 (10)	0.0938 (12)
O9	0.4620 (4)	−0.2891 (4)	0.49911 (11)	0.0952 (12)
O10	0.7598 (2)	0.1750 (2)	0.42863 (8)	0.0614 (9)
N4	0.2939 (3)	0.1676 (4)	0.40662 (11)	0.0617 (11)
N5	0.3840 (4)	−0.2228 (4)	0.48302 (11)	0.0669 (11)
N6	0.8109 (3)	−0.0414 (3)	0.43239 (9)	0.0503 (10)
H6A	0.7843	−0.1212	0.4356	0.060*
C9	0.5097 (3)	0.1061 (4)	0.42133 (11)	0.0452 (10)
H9A	0.5364	0.1806	0.4083	0.054*
C10	0.3841 (3)	0.0788 (4)	0.42467 (12)	0.0501 (11)
C11	0.3408 (4)	−0.0288 (4)	0.44465 (12)	0.0560 (11)
H11A	0.2558	−0.0460	0.4469	0.067*
C12	0.4279 (3)	−0.1087 (4)	0.46088 (11)	0.0481 (10)
C13	0.5549 (3)	−0.0875 (3)	0.45744 (11)	0.0468 (10)
H13A	0.6116	−0.1457	0.4683	0.056*
C14	0.5960 (3)	0.0213 (3)	0.43772 (11)	0.0390 (9)
C15	0.7307 (3)	0.0574 (3)	0.43282 (11)	0.0435 (10)
C16	0.9431 (3)	−0.0190 (4)	0.42662 (15)	0.0718 (14)
H16A	0.9863	−0.1025	0.4270	0.108*
H16B	0.9748	0.0372	0.4460	0.108*
H16C	0.9557	0.0234	0.4031	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.063 (2)	0.052 (2)	0.051 (3)	0.010 (2)	0.003 (2)	−0.001 (2)
C1	0.046 (2)	0.039 (2)	0.048 (3)	−0.0017 (18)	−0.004 (2)	−0.002 (2)
O1	0.082 (2)	0.064 (2)	0.093 (3)	−0.0010 (18)	0.012 (2)	−0.035 (2)
O2	0.0549 (19)	0.091 (2)	0.069 (2)	0.0238 (17)	0.0071 (17)	−0.0031 (19)
C2	0.052 (2)	0.038 (2)	0.049 (3)	0.0070 (19)	0.003 (2)	−0.001 (2)
N2	0.058 (2)	0.057 (2)	0.056 (3)	−0.012 (2)	−0.010 (2)	0.000 (2)
N3	0.0419 (17)	0.0308 (16)	0.098 (3)	−0.0009 (15)	−0.0010 (18)	0.007 (2)
O3	0.0486 (17)	0.091 (2)	0.078 (2)	−0.0116 (17)	−0.0149 (17)	0.003 (2)
C3	0.043 (2)	0.052 (2)	0.061 (3)	0.005 (2)	−0.003 (2)	0.009 (2)
O4	0.077 (2)	0.0621 (19)	0.085 (3)	−0.0036 (18)	−0.0174 (18)	−0.021 (2)
C4	0.042 (2)	0.042 (2)	0.055 (3)	−0.0048 (19)	−0.004 (2)	0.002 (2)
O5	0.0520 (16)	0.0334 (15)	0.106 (3)	0.0035 (13)	−0.0022 (17)	−0.0014 (15)
C5	0.048 (2)	0.040 (2)	0.043 (2)	−0.0008 (19)	0.0021 (19)	0.001 (2)
C6	0.042 (2)	0.034 (2)	0.048 (3)	0.0019 (18)	0.000 (2)	0.004 (2)
C7	0.054 (2)	0.031 (2)	0.049 (3)	0.001 (2)	0.001 (2)	0.001 (2)
C8	0.045 (2)	0.051 (2)	0.116 (4)	−0.001 (2)	0.000 (3)	0.002 (3)
O6	0.068 (2)	0.066 (2)	0.102 (3)	0.0145 (19)	−0.019 (2)	0.010 (2)
O7	0.0410 (17)	0.129 (3)	0.106 (3)	−0.0026 (19)	−0.0210 (18)	0.015 (2)
O8	0.072 (2)	0.117 (3)	0.092 (3)	−0.041 (2)	0.016 (2)	0.019 (2)
O9	0.099 (3)	0.079 (3)	0.108 (3)	−0.009 (2)	0.016 (2)	0.032 (2)
O10	0.0528 (16)	0.0324 (14)	0.099 (2)	−0.0012 (13)	0.0006 (17)	0.0076 (16)
N4	0.046 (2)	0.075 (3)	0.064 (3)	0.010 (2)	−0.016 (2)	−0.014 (2)
N5	0.073 (3)	0.069 (3)	0.058 (3)	−0.020 (2)	0.014 (2)	0.000 (2)
N6	0.0394 (17)	0.0264 (16)	0.085 (3)	−0.0011 (14)	0.0063 (17)	0.0019 (18)
C9	0.046 (2)	0.035 (2)	0.055 (3)	−0.0028 (18)	0.000 (2)	−0.003 (2)
C10	0.046 (2)	0.049 (2)	0.056 (3)	0.003 (2)	−0.008 (2)	−0.014 (2)
C11	0.051 (2)	0.061 (3)	0.055 (3)	−0.007 (2)	0.005 (2)	−0.009 (2)
C12	0.053 (2)	0.044 (2)	0.047 (3)	−0.010 (2)	0.009 (2)	0.001 (2)
C13	0.055 (2)	0.037 (2)	0.049 (3)	−0.0001 (19)	0.002 (2)	−0.004 (2)
C14	0.040 (2)	0.0296 (18)	0.047 (2)	0.0027 (17)	−0.0007 (18)	−0.0053 (19)
C15	0.048 (2)	0.027 (2)	0.056 (3)	−0.0007 (18)	−0.003 (2)	−0.0014 (19)
C16	0.045 (2)	0.049 (2)	0.121 (4)	−0.002 (2)	0.007 (3)	0.016 (3)

Geometric parameters (Å, º) top

N1—O1	1.207 (4)	O6—N4	1.224 (4)
N1—O2	1.229 (4)	O7—N4	1.221 (4)
N1—C2	1.475 (5)	O8—N5	1.214 (4)
C1—C2	1.378 (5)	O9—N5	1.217 (4)
C1—C6	1.386 (5)	O10—C15	1.232 (4)
C1—H1A	0.9300	N4—C10	1.468 (5)
C2—C3	1.387 (5)	N5—C12	1.475 (5)
N2—O4	1.221 (4)	N6—C15	1.314 (4)
N2—O3	1.221 (4)	N6—C16	1.449 (4)
N2—C4	1.491 (5)	N6—H6A	0.8600
N3—C7	1.325 (4)	C9—C10	1.379 (5)
N3—C8	1.446 (4)	C9—C14	1.391 (5)
N3—H3A	0.8600	C9—H9A	0.9300
C3—C4	1.374 (5)	C10—C11	1.381 (5)
C3—H3B	0.9300	C11—C12	1.364 (5)
C4—C5	1.366 (5)	C11—H11A	0.9300
O5—C7	1.234 (4)	C12—C13	1.383 (5)
C5—C6	1.385 (5)	C13—C14	1.378 (5)
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.498 (5)	C14—C15	1.498 (5)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600

O1—N1—O2	124.0 (4)	O7—N4—O6	123.5 (4)
O1—N1—C2	118.3 (3)	O7—N4—C10	117.8 (4)
O2—N1—C2	117.6 (4)	O6—N4—C10	118.7 (3)
C2—C1—C6	119.0 (3)	O8—N5—O9	124.3 (4)
C2—C1—H1A	120.5	O8—N5—C12	118.0 (4)
C6—C1—H1A	120.5	O9—N5—C12	117.7 (4)
C1—C2—C3	122.6 (4)	C15—N6—C16	121.6 (3)
C1—C2—N1	119.3 (4)	C15—N6—H6A	119.2
C3—C2—N1	118.1 (3)	C16—N6—H6A	119.2
O4—N2—O3	124.6 (4)	C10—C9—C14	119.4 (4)
O4—N2—C4	117.4 (3)	C10—C9—H9A	120.3
O3—N2—C4	118.0 (4)	C14—C9—H9A	120.3
C7—N3—C8	121.3 (3)	C9—C10—C11	122.0 (4)
C7—N3—H3A	119.3	C9—C10—N4	118.8 (4)
C8—N3—H3A	119.3	C11—C10—N4	119.2 (4)
C4—C3—C2	116.2 (3)	C12—C11—C10	117.1 (4)
C4—C3—H3B	121.9	C12—C11—H11A	121.4
C2—C3—H3B	121.9	C10—C11—H11A	121.4
C5—C4—C3	123.4 (4)	C11—C12—C13	122.9 (4)
C5—C4—N2	119.1 (4)	C11—C12—N5	118.2 (4)
C3—C4—N2	117.5 (3)	C13—C12—N5	118.9 (4)
C4—C5—C6	119.2 (4)	C14—C13—C12	119.0 (4)
C4—C5—H5A	120.4	C14—C13—H13A	120.5
C6—C5—H5A	120.4	C12—C13—H13A	120.5
C5—C6—C1	119.6 (3)	C13—C14—C9	119.6 (3)
C5—C6—C7	116.7 (3)	C13—C14—C15	124.2 (3)
C1—C6—C7	123.5 (3)	C9—C14—C15	116.2 (3)
O5—C7—N3	122.4 (3)	O10—C15—N6	123.9 (3)
O5—C7—C6	119.6 (3)	O10—C15—C14	119.4 (3)
N3—C7—C6	118.0 (3)	N6—C15—C14	116.6 (3)
N3—C8—H8A	109.5	N6—C16—H16A	109.5
N3—C8—H8B	109.5	N6—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
N3—C8—H8C	109.5	N6—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5

C6—C1—C2—C3	1.3 (6)	C14—C9—C10—C11	1.7 (6)
C6—C1—C2—N1	−178.8 (3)	C14—C9—C10—N4	−178.8 (3)
O1—N1—C2—C1	−2.9 (6)	O7—N4—C10—C9	172.6 (4)
O2—N1—C2—C1	177.6 (4)	O6—N4—C10—C9	−8.7 (6)
O1—N1—C2—C3	177.0 (4)	O7—N4—C10—C11	−7.8 (6)
O2—N1—C2—C3	−2.5 (5)	O6—N4—C10—C11	170.8 (4)
C1—C2—C3—C4	−0.4 (6)	C9—C10—C11—C12	−0.6 (6)
N1—C2—C3—C4	179.7 (3)	N4—C10—C11—C12	179.9 (4)
C2—C3—C4—C5	−1.0 (6)	C10—C11—C12—C13	−1.3 (6)
C2—C3—C4—N2	−178.6 (3)	C10—C11—C12—N5	178.8 (4)
O4—N2—C4—C5	−2.6 (6)	O8—N5—C12—C11	4.2 (6)
O3—N2—C4—C5	178.6 (4)	O9—N5—C12—C11	−175.9 (4)
O4—N2—C4—C3	175.1 (4)	O8—N5—C12—C13	−175.8 (4)
O3—N2—C4—C3	−3.8 (6)	O9—N5—C12—C13	4.1 (6)
C3—C4—C5—C6	1.4 (6)	C11—C12—C13—C14	2.0 (6)
N2—C4—C5—C6	178.9 (3)	N5—C12—C13—C14	−178.1 (3)
C4—C5—C6—C1	−0.3 (5)	C12—C13—C14—C9	−0.8 (5)
C4—C5—C6—C7	−176.4 (3)	C12—C13—C14—C15	178.3 (4)
C2—C1—C6—C5	−1.0 (5)	C10—C9—C14—C13	−0.9 (6)
C2—C1—C6—C7	174.8 (4)	C10—C9—C14—C15	179.9 (3)
C8—N3—C7—O5	−0.2 (7)	C16—N6—C15—O10	−0.3 (7)
C8—N3—C7—C6	−179.6 (4)	C16—N6—C15—C14	177.9 (3)
C5—C6—C7—O5	29.1 (5)	C13—C14—C15—O10	−151.0 (4)
C1—C6—C7—O5	−146.9 (4)	C9—C14—C15—O10	28.1 (5)
C5—C6—C7—N3	−151.5 (4)	C13—C14—C15—N6	30.6 (6)
C1—C6—C7—N3	32.5 (6)	C9—C14—C15—N6	−150.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5ⁱ	0.86	2.06	2.900 (4)	165
N6—H6A···O10ⁱ	0.86	2.12	2.955 (4)	164

Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₈H₇N₃O₅
M_r	225.16
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	10.716 (2), 10.057 (2), 36.101 (7)
V (Å³)	3890.6 (13)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.962, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	4711, 3402, 1653
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.162, 0.96
No. of reflections	3402
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5ⁱ	0.86	2.06	2.900 (4)	165.1
N6—H6A···O10ⁱ	0.86	2.12	2.955 (4)	164.0

Symmetry code: (i) −x+3/2, y−1/2, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (30940094) and the Science Foundation for Excellent Youth Scholars of the Education Commission of Hunan Province, China (10B077).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
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